Ryan Holiday was 19 years old when he dropped out of college at UC Riverside – just after meeting his now-wife Samantha there - to apprentice under Robert Greene, author of The 48 Laws of Power. He embarked on a career in marketing, as Director of Marketing at American Apparel and then founder of a creative agency, before settling into his current careers as an author, podcaster, philosopher and bookstore owner, one that has culminated in him being referred to as the modern godfather of ancient philosophy.
Ryan is the author of more than a dozen books, including The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic and The Daily Dad, which have sold millions of copies in thirty languages. His The Daily Stoic emails ‘designed to help you cultivate strength, insight, and wisdom to live your best life’ go to over 300,000 people each day and his podcast of the same name stretches his reach even wider. He hosts a second podcast, The Daily Dad, where Samantha is a frequent guest.
Ryan and Samantha, who goes by Sam, met 17 years ago and have been married for nine. They live on a ranch outside of Austin with their two sons, 8 and 5 years old - and two donkeys, 15 cows, two rabbits, a tortoise and three toads. Sam says they also share their place with a few animals they don’t own, including a cat, wild boars, deer, turkeys and raccoons – that Sam admits to feeding (we don’t recommend it to others!)
They said they moved to the Austin-area because they lived all over the country, loved New Orleans, loved New York and loved Los Angeles and feel like Austin has a mix of all of those cities. And then they moved to the ranch because, “At some point, we decided that if we were going to live in Texas, we should live in Texas. It's slower. It's quiet,” Sam says. “We can see the stars every night. We live on a dirt road--it's like going back in time.“
They also own a perfect little bookstore in Bastrop called The Painted Porch Book Shop. “It was Sam's crazy idea one morning as we sat across the street eating breakfast at Maxine's--a great diner in Bastrop,” Ryan says. “It was probably a crazy idea under normal circumstances, but we bought the buildings and then started construction the first week of March 2020.” He says the most rewarding part about owning the bookstore is that “Almost everything is digital these days. Even most book sales are digital--audiobooks, ebooks and Amazon and it's very rewarding to do something that is physical, that exists. To have a space not just for ourselves but for everyone in town, for people passing through, to be able to display stuff we love and want people to know about.” Sam adds, “Being able to find the right book for someone is just a wonderful feeling.”
Ryan and Sam both have their offices in the same building and and it's where Ryan records his podcasts as well. He says the biggest challenge to owning a bookstore is “It’s the same amount of work as an online business--maybe more--but it's only going to be so big. It's not a way to get rich, that's for sure.”
The couple are also relatively new owners of Bastrop staple Tracy’s Drive-In Grocery, a personal passion of Sam’s. Austin Lifestyle spent an afternoon in Bastrop with the Holidays in the run up for the holidays to learn more about them, their holiday traditions, book recommendations for everyone on your list, and what Ryan has learned that can help you set yourself up for success going into the near year.
Ryan…
You host a popular podcast and blog, write best-selling books, do speaking engagements and have a marketing consulting company– and a bookstore. Which brings you the most joy to do?
I'm happy to do all of it but you become a writer to write. One of the tricky things about all these technologies and platforms is that they take away from the time you'd get to spend doing the thing you love. I really have to try to stay disciplined or you can wake up one day and wonder why I'm not producing pages anymore.
You’ve written 12 books, what’s your process when writing a book?
A few crappy pages a day turns into an editable manuscript and eventually an edited manuscript turns into a published book.
Do you have ideas for your next one or few?
I've spent the last five years on a four-book series on the cardinal virtues. I did Courage in 2020, Discipline in 2021, Justice in 2023 and hopefully I will finish Wisdom before the end of the year.
If people were going to read one of your books, which do you think would be the most impactful? Which one should the start with?
This is always so hard because you love all of them, and secretly hope your latest is your best, but I think if someone is looking to start with Stoicism, The Daily Stoic or if they're a parent, The Daily Dad.
Going into the new year, what are a few things you’ve written about that people can do to set themselves up for success to be a better version of themselves than they were in 2024?
Every year for Daily Stoic we do a big challenge called New Year New You which is three weeks of Stoic-inspired challenges to kick off the year--and they are challenges, like hard stuff built around Stoic practices. It's something we spend a big chunk of the year working on and have thousands of people participate in from all over the world. Having done it now for 6 years, I get so much out of it and from the community.
What are some of your holiday traditions?
When you have retail businesses, you think about this season a little differently. It's all hands on deck. But, our biggest family tradition is in November -since we have several birthdays. We get a cake for each party and after everyone has a slice, we go out into the front yard and have a food fight with the rest.
Sam…
Would you add anything to holiday traditions?
Cutting down a Christmas Tree in Elgin and going to look at Christmas lights along the river and to the holiday parade in Bastrop. It's really nostalgic and the whole town turns out for it.
What drew you to purchase Tracy’s Drive-In Grocery Store?
Tracy's has been in the same spot, doing the same thing for almost 80 years. It's not fancy. It's not huge. But it means something to people and it's a place they depend on.
What do you love about Tracy’s?
It embodies everything that's great about a small town. It's connected. It's fun. It's always the home of absurd drama and strong opinions. The coffee is good and the company is better.
You’re head of operations for the bookstore, The Daily Stoic, Tracy’s and do school drop offs/pick-ups every day – how do you do it all?
One of these places sells coffee. It's fine.
How much do you read?
Always. It's our job! Thinking about reading that way really helps us prioritize and teach the importance of doing so to our kids!
Which of Ryan’s books have you personally found most impactful?
I live with him, do I also have to read his books?
How do you choose what books to sell in the bookstore?
Maybe it's not the best business decision but we only carry books that we like and that we've actually read. A typical bookstore of our size would ordinarily have 4-5 times as many books, but our approach is just have stuff we'd feel confident recommending--books we know people will enjoy. We're not ordering every new title. In fact, we have to do a lot of work to keep some of our older titles in stock because they aren't what publishers always care about.
Books are the best gifts. Here are Sam’s recs for books to buy the people on your list in a dozen different categories.
Person on a self-improvement journey: Robert Greene's Mastery or Meditations
Lover of thrillers: I'd go back to the basics with Agatha Christie or Raymond Chandler (LA Noir mysteries) for traditional books in this category but Tunnel 29 or The Art Thief are two narrative non-fiction that will have readers thriller level stressed.
Lover of historical fiction: Kristin Hannah
For kids: Greeking Out, the Dragon Masters series, Nature's Treasures: Tales of More Than 100 Extraordinary Objects from Nature
For tweens: Hatchet, Percy Jackson, Midnight Children
For teens: The Selection series, Unwind Series and The Hunger Games is still going strong.
Parenting book: Good Inside by Dr Becky Kennedy
Texas book: Goodbye to a River by John Graves
Travel Book: Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel
For runners: What I Talk About When I Talk About Running by Haruki Murakami
Fantasy: Eaters of the Dead by Michael Crichton
Romance: A Deal with the Bossy Devil by Kyra Parsi and everything Mariana Zapata, Just for the Summer by Abby Jimenez
Fantasy romance: Sarah J Maas, of course, and as a gift there are special editions of A Court of Thorns and Roses and Throne of Glass
There are too many just send people to me!
You can find Sam on Instagram at @paintedporchbookshop
Or Email her at @paintedPorchBookshop@gmail.com
Follow Ryan Holiday on Instagram @ryanholiday and @dailystoic and @dailydad. Sign up for his newsletter at DailyStoic.com
The Painted Porch Book Shop: 912 Main St, Bastrop, TX 78602
“Books are door-shaped portals carrying me across oceans and centuries, helping me feel less alone." -Margarita Engle (the Holidays' favorite quote)